A new approach to the synthesis of linear polyhydroxy polynuclear aromatic systems is being developed. Ultimately, the developed methodology will be applied to the synthesis of anthracycline antibiotics with potent biological properties. An ortho-substituted aromatic ring with methyl and carboethoxy functionalities, which are used to construct a new ring, serves as the template. During formation of the second ring, functionalities identical to those initially used are regioselectively built on the new aromatic ring. At present we have developed a route in which the ortho-substituents are initially converted to a 3-methyl isocoumarin fragment. Reformatsky reaction with ethyl bromoacetate on the isocoumarin completes the aromatic ring annelation and also recontructs the ortho methyl and carboethoxy functionalities. Using the repetitive ring construction method we have successfully completed the synthesis of a naphthalene precursor and are presently pursuing the synthesis of an anthracene intermediate which will be used to construct the anticancer antibiotics, Kidamycins, Daunomycin and Adriamycin.